Edeson, S.J., Jiang, J., Swanson, S. et al. (4 more authors) (2014) Studies on the stereochemical assignment of 3-acylidene 2-oxindoles. Organic and Biomolecular Chemistry, 12 (20). 3201 - 3210. ISSN 1477-0520
Abstract
The designation of E/Z-geometrical isomers in 3-acylidene 2-oxindoles by NMR spectroscopy can lead to erroneous assignment of alkene stereochemistry because of the narrow chemical shift range observed over a large series of analogues. In contrast, UV-Vis spectroscopy offers a convenient and more reliable method for alkene stereochemical assignment. A combination of X-ray crystallography and theoretical studies shows that the observed differences in UV-Vis spectroscopic behaviour relate to the twisted conformation of the Z-isomers that provides reduced conjugation and weaker hypsochromic (blue-shifted) absorbances relative to those of the E-isomers.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2014 The Author(s). This is an Open Access article distributed under the terms of the Creative Commons Attribution Licence (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 20 Jun 2014 13:18 |
Last Modified: | 20 Jun 2014 13:18 |
Published Version: | http://dx.doi.org/10.1039/c4ob00496e |
Status: | Published |
Publisher: | RSC Publishing |
Refereed: | Yes |
Identification Number: | 10.1039/c4ob00496e |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:79460 |